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Copper Catalyzed Oxidative Arylation of Tertiary Carbon Centers

Prakash Basnet, Melissa B. Sebold, Charles E. Hendrick, Marisa C. Kozlowski

2020Organic Letters20 citationsDOIOpen Access PDF

Abstract

catalyzed oxidative arylation of a tertiary carbon-containing substrate including aryl malononitriles, 3-aryl benzofuran-2-ones, and 3-aryl oxindoles. In some cases, the nitrile groups of the aryl malononitriles undergo further reactions leading to lactones or imines. These reaction conditions are applicable for a range of arenes, including phenols, anilines, anisoles, and heteroarenes. Mechanistic studies support the formation of a cationic intermediate via a two-electron oxidation.

Topics & Concepts

ChemistryArylNitrileCatalysisCationic polymerizationOxidative phosphorylationBenzofuranPhenolsCarbon fibersSubstrate (aquarium)Organic chemistryMedicinal chemistryCombinatorial chemistryOceanographyAlkylMaterials scienceComposite materialGeologyBiochemistryComposite numberCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsRadical Photochemical Reactions
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